that first email

Reader O. C. writes:

I joined an online dating site recently and I’m wondering what kind of first emails get the most responses. Can you help a guy out?

Dear O.C.:

In honor of your question, I went through one of my inboxes to see who I responded to and who I didn’t. And now I’m going to make a list of DO’s and DON’T’s because I haven’t in a while.


what to write what to write

Image: Michelle Meiklejohn / FreeDigitalPhotos.net


Spell check. It’s not hard. Copy and paste the whole thing into your word processor before you send it. While I’ll give a guy a chance if he uses “your” where “you’re” should be, I don’t give him the chance without wincing. Furthermore, if he has major spelling errors in a one-line email, there is absolutely no way I’m going to respond. This is like a cover letter. If you want the job, you put your best face forward and you check the grammar. Make it look like you care at least slightly how you’re represented.

Write about something from her dating profile. Take something that struck you as interesting and write about it. Girls like to hear about themselves, and they like to think you’re paying attention.

Ask a question. That way she has a reason to respond. When a guy writes “hey liked your profile we should hang”, I never know what to write back. “Thanks” is about all that comes to mind. Make it look like you took the time to read her profile and you’re actually interested. You can pretty much be sure she’s not going to be totally taken in by your photos unless you are beyond Brad Pitt smokingly hot, in which case the girls would be contacting you.

Sign it with your first name. If you’re comfortable doing that, giving her your actual name is a great way to set yourself apart. Especially since most user names are things like “FunkyChkn4U”; they blend together after a while.

Attach a photo if the system allows it. Make sure it’s your best photo, and make sure it’s one of your face.

Keep it short. Three lines is probably good — a brief introduction about what struck you (and why not discuss how much you like it, too?), a question about her, your name.

Be funny. If you can.


Use text speak. Srsly. Write in complete words and sentences. U don’t want 2 luk stupid LOL.

Give her your “real” email address or phone number. Not in the first email, at least. That can come later. It makes you look desperate if you send it too soon.

Invite her to go out immediately. You don’t know if you really want to do that yet. Wait until the third or fourth email. Chat with her on IM first. Get a feel for her personality.

Talk about sex, or make sexually charged comments. Even if they’re funny. Unless she’s specifically asked for sex, don’t offer it. You’re just stereotyping yourself.

Attach a photo of just your body or certain naughty bits. Girls don’t want that in an introduction, unless they’re just looking for sex. If she hasn’t explicitly asked for a body shot or a hoohaa shot, don’t send it.

Criticize her profile. Or her user name. Or her photos. Or anything else. At all. It’ll make her mad, not interested, in spite of how that “little insult” is supposed to work in real life (if your name is Mystery and you write books about being a pick up artist, of course).

Send a follow up email asking why she hasn’t responded. If she doesn’t write back, she’s not interested. Take the rejection like a man and move on. Even after you’ve had a few email convos already, sending repetitive emails is annoying. Let it go.

If my advice wasn’t good enough, check out OkCupid’s blog on the whole subject. They even have data to back it up, so you don’t have to trust my feminine instincts.


5 Responses to “that first email”

  1. 1 VMM
    October 20, 2010 at 4:30 pm

    But where do you fall on the use of emoticons? In my prolific match.com days, I don’t think I ever responded to a first email that used one. Too harsh?

    • October 20, 2010 at 4:32 pm

      Generally, I approve of a smile or a wink in an email, but not something weird like a dancing pickle or weird alien face. If it helps get your point across, use the emoticon. If it’s extraneous, don’t. Mostly for men I would say err on the side of caution with the emoticons. They could detract from your message, and people like VMM won’t write back. 🙂

    • 3 Brian
      October 21, 2010 at 11:01 am

      Unless it is obsessive, I would consider that to be overly harsh. I can’t remember if I used them or not, but I think this is one of those things that drive guys nuts. Some women are quick to judge based on things that have no real reflection on how good of a partner they are for you. How is a guy supposed to know a smiley negates the fact he has a Masters, runs in marathons, volunteers to save puppies, and cured cancer?

  2. 4 Richard
    October 20, 2010 at 5:23 pm

    I agree with all of Kat’s advice, but have a bit more to add.

    Firstly, pace yourself. Send no more than one introductory email a day and plan to quickly back off to a couple a week. If you truly take Kat’s advice, you’ll probably have a high response rate. Too many parallel e-conversations will drive you nuts and suck up all your free time.

    Pace your responses. Respond once or twice a day unless you want to make a career out of e-flirting.

    Ask for a face-to-face meeting after three or four days/emails. You don’t want to spend too much time leading a lady on only to discover no personal attraction once you finally meet. Special note: when you do meet a woman, ALWAYS practice good behavior and charm. Later, if there really is no attraction, be a gentleman, thank her for her time and conversation, and tell her that she’s wonderful but that you think you both have better matches out there.

    Finally, keep notes. Print out those profiles and write notes on them. Should you need them, you’ll really need them.

    Erratum: If an otherwise literate woman has an obviously unintentional syntax/spelling/grammar error in her profile, be polite and gently point it out. She may resent you, but she’ll fix it and better impress the next guy. If she has a factual error, well, that’s an opening for a joke or pun.

  3. 5 Consuelo
    October 20, 2010 at 6:54 pm

    Can I be a shallow guy and point out some things women can do (and I suppose some guys too)? OK good, thanks.

    1. POST A FULL BODY PHOTO. I know, I know, this is ridiculously shallow but guys are visual creatures. It’s entirely possible that you are overweight and will get a date with a guy who generally likes more average or fit sized ladies and maybe maybe you will woo him with your amazingly charming personality. But let’s join the real world and say this probably doesn’t happen too often. You don’t have to be in a bathing suit or anything, but just a photo from the knees up in something slightly more form fitting than a potato sack should do the trick. Which leads me to my next point…

    2. OVERWEIGHT DOESN’T MEAN “CURVY” OR “AVERAGE” If your body leans more towards Rosie O’Donnell than Marilyn Monroe, I’m sorry but you are probably “a few pounds extra” or “large and in charge” (or whatever term the dating site has for it).

    3. IF YOU ARE ATTRACTIVE, SHOW OFF THAT CUTE FACE. Sometimes gals will put cryptic photos of their toes or hair or butt or whatever. I’m guessing this is a ploy to get guys interested in them, so they can then send them a photo of their face after luring said dude in. Nearly all of the time Ms. Cryptic Photos tends to be rather unattractive, so it just leaves Mr. Lured In Dude frustrated and you dateless. This is different than not having photos up on a dating site because of privacy or embarrassment issues which is perfectly reasonable.

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